My wife and I hope to travel more frequently in retirement, and we would like to try some educational trips, if possible. Any suggestions? Any groups or firms that specialize in this type of travel?

Start with Road Scholar (roadscholar.org), which, in the mid-1970s, all but invented the idea of educational travel for older adults. The Boston-based organization offers about 5,500 tours in all 50 states and 150 countries. Among the most popular: seeing western Canada by train; island hopping in Greece; and exploring Yosemite National Park in California.

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We also are big fans of Cornell University’s Adult University in Ithaca, N.Y. (Go to sce.cornell.edu and click on: Cornell’s Adult University.) Each July, the school offers, in effect: a two-fer: some two-dozen courses, each lasting about six days, that dive into a variety of subjects and activities (art, politics, food, wine and kayaking, among others), and the opportunity to explore the Finger Lakes region.

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Your account custodian likely has an “IRA Distribution Form” (or something with a similar title) that will need to be filled out. In most cases, the same form is used for withdrawals from various types of individual retirement accounts. Among the information required: the type of distribution (more about this in a moment), the amount to be withdrawn, and where the money should go. A financial adviser should be able to help you with this process, if need be.

Less simple are the rules that cover Roth withdrawals. Take the type of distribution: Is it a “qualified” distribution? (Meaning, at a minimum, that the account is at least five years old.) And what about the funds inside the account? Are they simply contributions that you have made—or does the account also include amounts converted from a traditional IRA or retirement plan? (If so, a withdrawal could be more complicated.)

I have been collecting Social Security benefits for some years now. My wife won't reach retirement age for another seven years. Is it possible for her to claim a spousal benefit until she reaches her retirement age?

The youngest age at which most people can claim Social Security—whether it’s a benefit based on their own earnings record or a spousal benefit—is 62. (One notable exception: surviving spouses. A widow or widower can claim benefits as early as age 60; a disabled widow or widower can claim as early as age 50.)

So, if your wife has reached 62, she can file for Social Security. If she hasn’t reached age 62, she wouldn’t be able to collect a spousal benefit while she is waiting to reach her retirement age.

As I understand it, 2015 contributions to a Roth IRA can be made as late as April 15, 2016. If I transfer money from a traditional IRA into a Roth IRA on April 1, 2016, do I pay federal income taxes on this IRA redemption on my 2015 or 2016 taxes?

You might be confusing “contributions” and “conversions,” two concepts that can trip up people at tax time.

Let’s start with contributions. A wrinkle in the tax laws gives people about 15 months to make a contribution to an IRA for a particular tax year. So, for tax year 2015, you have from Jan. 1, 2015, to April 18, 2016, to make a contribution to your Roth. (Normally, the deadline is April 15, the due date for your federal tax return. But the Internal Revenue Service has pushed the filing date this year to April 18.) Depending on your income, the maximum contribution for 2015 is $5,500. People age 50 and older can contribute as much as $6,500.

By contrast, the deadline for a Roth conversion—a transfer of funds to a Roth from a traditional IRA—is Dec. 31. So, if you transfer money to your Roth on April 1, that transaction (and any tax due) would be reflected on your tax return for 2016.

My husband and I—ages 66 and 63, respectively—are both retired. My husband claimed his Social Security benefits at age 62. I plan to claim my benefits at my full retirement age of 66. I will be required to go on Medicare at age 65 and pay Medicare premiums. Am I eligible to claim a spousal benefit at age 65 to cover my Medicare premiums, and then claim my own benefits at 66 or later?

Short answer: You can’t do this.

If you claim benefits at age 65—before your “full retirement age,” as defined by the Social Security Administration—the agency will look at two numbers: the size of your benefit based on your earnings record, and the size of your spousal benefit (given that your husband is already collecting Social Security). At this point, the agency will automatically award you the larger of those two benefits. Period. You don’t get a say in the matter. And after that determination has been made, you won't be able to switch to a different benefit down the road.

This is what’s known as the “deemed filing” rule. In other words, if you apply for benefits before reaching your full retirement age, you are required or “deemed” to file (according to the Social Security Administration) for all benefits that you might qualify for.

But…if you wait until your full retirement age of 66, you would have a choice of benefits. You could claim just a spousal benefit and then switch to your benefit (based on your work record) at some point in the future. (Say, age 70.) This would allow your benefit to increase in size, thanks to “delayed retirement credits.”

This is known as a “restricted application”—filing for just a spousal benefit at one’s full retirement age. And you are eligible to do this, even under the new Social Security rules. (A person had to reach age 62 before the end of 2015 to be eligible for a restricted application in the future.)

Planning for retirement can be a daunting process that raises a host of questions. So we have introduced Ask Encore as a regular feature in the Investing in Funds & ETFs and Wealth Management reports. Written by Glenn Ruffenach, a former reporter and editor for The Wall Street Journal, and co-author of “The Wall Street Journal Complete Retirement Guidebook,” the column examines financial issues for those thinking about, planning and living their retirement. We welcome your questions and comments at askencore@wsj.com.

Appeared in the March 28, 2016, print edition as 'Where Retirees Can Find Ideas for Educational Travel.'

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